Can I get pregnant from anal sex? Again, he should be very slow and cautious doing this, following your instructions and feedback to either continue, slow down, stop or slowly pull out. Many couples talk about these kinds of things indirectly and never fully express their wants and needs. Get her worked up by getting her close and backing off a couple times until she is ready to explode!!! He needs to apply a bit lube to the tip of his finger and some more to your ass. One man can choose to enter her anus while placing his hands firmly on her buttocks.